4-Chlorophenol → HCID 89544319, compound

HRID 2203414Notes

Reaction equation

HRID 2203414 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:16][C:17]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:18]=1[S:25](Cl)(=[O:27])=[O:26]>O1CCCC1.C(OCC)(=O)C.O>[F:16][C:17]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:18]=1[S:25]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:27])=[O:26]

Participants

7

Reactant 3

HCID 46844-ChlorophenolHCID 8471TriethylamineHCID 27769792,4,5-Trifluorobenzenesulfonyl chloride

Product 1

HCID 89544319HCID 89544319, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-chlorophenol (13.94 g, 108 mmol) in tetrahydrofuran (400 mL) at ambient temperature was added triethylamine (30.2 mL, 216 mmol). The mixture was stirred at ambient temperature for 10 minutes and cooled to 0° C. 2,4,5-Trifluorobenzenesulfonyl chloride (25.00 g, 108 mmol) was added and the reaction mixture was stirred for 1 h at ambient temperature and diluted with ethyl acetate (600 mL) and water (200 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford 4-chlorophenyl 2,4,5-trifluorobenzenesulfonate as a colorless liquid in 98% yield (34.4 g): 1H NMR (300 MHz, DMSO-d6) δ8.18-7.96 (m, 2H), 7.50 (d, J=7.2 Hz, 2H), 7.19 (d, J=7.2 Hz, 2H).

Workup

  1. temperaturecooled to 0° C
  2. stirringthe reaction mixture was stirred for 1 h at ambient temperature
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4c3d64d9a1b54b64a817b5ace8bc3d58
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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